A novel iodomethylene-dimethyl-dihydropyranone induces G2/M arrest and apoptosis in human cancer cells.

Background: The putative pharmacophore of a naturally cytotoxic limonoid haperforin B1, E-5-iodomethylene-6,6-dimethyl-5,6-dihydropyran-2-one (IDDP) was synthesized and its biological activity was investigated.

Materials And Methods: The cytotoxicity of IDDP was assessed using human breast, lung, colorectal and epidermal carcinomas, chronic myeloid leukemia and glioblastoma cell lines. Cell cycle analysis was performed by flow cytometry.

New rearranged limonoids from Harrisonia perforata. III.

Three new limonoids, named haperforins C2 (1), F (2), and G (3), were isolated from a sample of Harrisonia perforata leaves collected in Central Vietnam. Their structures were determined by single-crystal X-ray diffraction analyses, and their NMR and mass spectral data are reported.

New rearranged limonoids from Harrisonia perforata.

Two new rearranged limonoids, named haperforine A (1) and haperforine E (2), were isolated from a sample of Harrisonia perforata leaves collected in Center Vietnam and their structures determined by X-ray diffraction analysis. The structure of a minor compound was established as 12-desacetylhaperforine A (3) by chemical correlation. Their NMR and mass spectroscopic properties are reported.

Total Synthesis of (-)-Maytansinol.

A total synthesis of maytansinol (1) was achieved, in a convergent way, using (3S,6S,7S)-aldehyde 4 and (S)-p-tolyl sulfoxide 3 as fragments. When the anion of 3 was condensed with aldehyde 4, some induction at C(10) was observed (60% de), giving the C(1)-N(19)-open-chain compound 7, after thermal elimination of sulfinate. Pure E/E stereochemistry of the 11,13-diene was obtained.